3-(4-chloro-benzylamino)propionic acid methyl ester | 4063-30-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(4-chloro-benzylamino)propionic acid methyl ester
• 英文别名: 3-(4-Chloro-benzylamino)-propionic acid methyl ester；methyl 3-[(4-chlorophenyl)methylamino]propanoate
• CAS: 4063-30-3
• 化学式: C₁₁H₁₄ClNO₂
• mdl: MFCD11176950
• 分子量: 227.691
• InChiKey: CHRQVZKXDGGIPE-UHFFFAOYSA-N

物化性质

• 沸点：
  103-111 °C(Press: 0.3 Torr)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-chloro-benzylamino)propionic acid methyl ester 在 盐酸 、 sodium methylate 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 23.0h， 生成 1-(4-Chlorobenzyl)piperidine-2,4-dione
  参考文献：
  名称：

  II. SAR studies of pyridyl–piperazinyl-piperidine derivatives as CXCR3 chemokine antagonists

  摘要：

  The structure-human CXCR3 binding affinity relationship of a series of pyridyl-piperazinyl-piperidine derivatives was explored. The optimization campaign highlighted the pronounced effect of 2'-piperazine substitution on CXCR3 receptor affinity. Analog 18j, harboring a 2'(S)-ethylpiperazine moiety, exhibited a human CXCR3 IC(50) of 0.2 nM. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.114
• 作为产物：
  描述：

  对氯苄胺 、 丙烯酸甲酯（MA） 以 甲醇 为溶剂， 反应 16.0h， 以98%的产率得到3-(4-chloro-benzylamino)propionic acid methyl ester
  参考文献：
  名称：

  II. SAR studies of pyridyl–piperazinyl-piperidine derivatives as CXCR3 chemokine antagonists

  摘要：

  The structure-human CXCR3 binding affinity relationship of a series of pyridyl-piperazinyl-piperidine derivatives was explored. The optimization campaign highlighted the pronounced effect of 2'-piperazine substitution on CXCR3 receptor affinity. Analog 18j, harboring a 2'(S)-ethylpiperazine moiety, exhibited a human CXCR3 IC(50) of 0.2 nM. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.114

文献信息

• [EN] AZETIDINE DERIVATIVES USEFUL FOR THE TREATMENT OF METABOLIC AND INFLAMMATORY DISEASES<br/>[FR] DÉRIVÉS D'AZÉTIDINE UTILES POUR LE TRAITEMENT DE MALADIES MÉTABOLIQUES ET INFLAMMATOIRES
  申请人：GALAPAGOS NV

  公开号：WO2012098033A1

  公开（公告）日：2012-07-26

  Compounds are disclosed that have a formula represented by the following: These compounds may be prepared as a pharmaceutical composition, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example inflammatory conditions, infectious diseases, autoimmune diseases, diseases involving impairment of immune cell functions, cardiometabolic diseases, and/or proliferative diseases.

  披露了具有以下表示的公式的化合物：这些化合物可以制备为药物组合物，并可用于预防和治疗包括人类在内的哺乳动物的各种疾病，例如炎症性疾病、传染病、自身免疫疾病、涉及免疫细胞功能受损的疾病、心脏代谢疾病和/或增殖性疾病，举例不限。
• NOVEL COMPOUNDS USEFUL FOR THE TREATMENT OF METABOLIC AND INFLAMMATORY DISEASES
  申请人：Sanière Laurent Raymond Maurice

  公开号：US20130303515A1

  公开（公告）日：2013-11-14

  Compounds are disclosed that have a formula represented by the following: These compounds may be prepared as a pharmaceutical composition, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example inflammatory conditions, infectious diseases, autoimmune diseases, diseases involving impairment of immune cell functions, cardiometabolic diseases, and/or proliferative diseases.

  公开了具有以下式子表示的化合物：这些化合物可以制备成药物组合物，并可用于哺乳动物，包括人类的预防和治疗，例如炎症性疾病、传染病、自身免疫疾病、涉及免疫细胞功能受损的疾病、心脏代谢疾病和/或增殖性疾病等。
• Compounds useful for the treatment of metabolic and inflammatory diseases
  申请人：Sanière Laurent Raymond Maurice

  公开号：US08759334B2

  公开（公告）日：2014-06-24

  Compounds are disclosed that have a formula represented by the following: These compounds may be prepared as a pharmaceutical composition, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example inflammatory conditions, infectious diseases, autoimmune diseases, diseases involving impairment of immune cell functions, cardiometabolic diseases, and/or proliferative diseases.

  揭示了具有以下公式表示的化合物：这些化合物可以制备为药物组合物，并可用于哺乳动物，包括人类的预防和治疗各种疾病，例如炎症性疾病、传染病、自身免疫疾病、涉及免疫细胞功能受损的疾病、心血管代谢疾病和/或增殖性疾病，举例而言。
• Discovery and Optimization of an Azetidine Chemical Series As a Free Fatty Acid Receptor 2 (FFA2) Antagonist: From Hit to Clinic
  作者：Mathieu Pizzonero、Sonia Dupont、Marielle Babel、Stéphane Beaumont、Natacha Bienvenu、Roland Blanqué、Laëtitia Cherel、Thierry Christophe、Benedetta Crescenzi、Elsa De Lemos、Philippe Delerive、Pierre Deprez、Steve De Vos、Fatoumata Djata、Stephen Fletcher、Sabrina Kopiejewski、Christelle L’Ebraly、Jean-Michel Lefrançois、Stéphanie Lavazais、Murielle Manioc、Luc Nelles、Line Oste、Denis Polancec、Vanessa Quénéhen、Florilène Soulas、Nicolas Triballeau、Ellen M. van der Aar、Nick Vandeghinste、Emanuelle Wakselman、Reginald Brys、Laurent Saniere

  DOI：10.1021/jm5012885

  日期：2014.12.11

  FFA2, also called GPR43, is a G-protein coupled receptor for short chain fatty acids which is involved in the mediation of inflammatory responses. A class of azetidines was developed as potent FFA2 antagonists. Multiparametric optimization of early hits with moderate potency and suboptimal ADME properties led to the identification of several compounds with nanomolar potency on the receptor combined with excellent pharmacokinetic (PK) parameters. The most advanced compound, 4-[[(R)-1-(benzo[b]thiophene-3-carbonyl)-2-methyl-azetidine-2-carbonyl]-(3-chloro-benzyl)-amino]-butyric acid 99 (GLPG0974), is able to inhibit acetate-induced neutrophil migration strongly in vitro and demonstrated ability to inhibit a neutrophil-based pharmacodynamic (PD) marker, CD11b activation-specific epitope [AE], in a human whole blood assay. All together, these data supported the progression of 99 toward next phases, becoming the first FFA2 antagonist to reach the clinic.
• PIPERIDINE/PIPERAZINE DERIVATIVES
  申请人：Janssen Pharmaceutica, N.V.

  公开号：EP2152270A1

  公开（公告）日：2010-02-17